DE2509049A1 - Neue substituierte n-acyl-n''-(3-amino-2-cyano-acryloyl)-formamidrazone, verfahren zu ihrer herstellung und sie enthaltende arzneimittel - Google Patents
Neue substituierte n-acyl-n''-(3-amino-2-cyano-acryloyl)-formamidrazone, verfahren zu ihrer herstellung und sie enthaltende arzneimittelInfo
- Publication number
- DE2509049A1 DE2509049A1 DE19752509049 DE2509049A DE2509049A1 DE 2509049 A1 DE2509049 A1 DE 2509049A1 DE 19752509049 DE19752509049 DE 19752509049 DE 2509049 A DE2509049 A DE 2509049A DE 2509049 A1 DE2509049 A1 DE 2509049A1
- Authority
- DE
- Germany
- Prior art keywords
- group
- cyano
- acryloyl
- acyl
- amino
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Pending
Links
- 238000000034 method Methods 0.000 title claims description 26
- 238000004519 manufacturing process Methods 0.000 title description 4
- BBUAPPCGKDGBDN-UHFFFAOYSA-N N',4-diamino-3-cyano-2-oxobut-3-enimidamide Chemical compound NC=C(C(=O)C(=N)NN)C#N BBUAPPCGKDGBDN-UHFFFAOYSA-N 0.000 title 1
- 229940126601 medicinal product Drugs 0.000 title 1
- 150000001875 compounds Chemical class 0.000 claims description 52
- 150000003839 salts Chemical class 0.000 claims description 47
- -1 4- [N, N-Dipropyl-sulfamoyl] -phenyl Chemical group 0.000 claims description 35
- 125000004432 carbon atom Chemical group C* 0.000 claims description 21
- 150000007522 mineralic acids Chemical class 0.000 claims description 21
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- 239000003814 drug Substances 0.000 claims description 15
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 14
- 239000004480 active ingredient Substances 0.000 claims description 10
- 238000006243 chemical reaction Methods 0.000 claims description 10
- BDAGIHXWWSANSR-UHFFFAOYSA-N methanoic acid Natural products OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 claims description 10
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 10
- 150000008064 anhydrides Chemical class 0.000 claims description 9
- 238000002360 preparation method Methods 0.000 claims description 9
- 201000005569 Gout Diseases 0.000 claims description 8
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- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 7
- 125000000217 alkyl group Chemical group 0.000 claims description 6
- 125000004076 pyridyl group Chemical group 0.000 claims description 6
- 239000007858 starting material Substances 0.000 claims description 6
- OSWFIVFLDKOXQC-UHFFFAOYSA-N 4-(3-methoxyphenyl)aniline Chemical compound COC1=CC=CC(C=2C=CC(N)=CC=2)=C1 OSWFIVFLDKOXQC-UHFFFAOYSA-N 0.000 claims description 5
- 125000002947 alkylene group Chemical group 0.000 claims description 5
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- NWZSZGALRFJKBT-KNIFDHDWSA-N (2s)-2,6-diaminohexanoic acid;(2s)-2-hydroxybutanedioic acid Chemical compound OC(=O)[C@@H](O)CC(O)=O.NCCCC[C@H](N)C(O)=O NWZSZGALRFJKBT-KNIFDHDWSA-N 0.000 description 2
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- 239000000047 product Substances 0.000 description 1
- WYVAMUWZEOHJOQ-UHFFFAOYSA-N propionic anhydride Chemical compound CCC(=O)OC(=O)CC WYVAMUWZEOHJOQ-UHFFFAOYSA-N 0.000 description 1
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 235000013772 propylene glycol Nutrition 0.000 description 1
- 238000000746 purification Methods 0.000 description 1
- 230000004144 purine metabolism Effects 0.000 description 1
- 150000003212 purines Chemical class 0.000 description 1
- 229940079877 pyrogallol Drugs 0.000 description 1
- 239000000376 reactant Substances 0.000 description 1
- 230000035484 reaction time Effects 0.000 description 1
- 238000007363 ring formation reaction Methods 0.000 description 1
- 125000002914 sec-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- 125000003548 sec-pentyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- 238000000926 separation method Methods 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 239000003381 stabilizer Substances 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 125000001424 substituent group Chemical group 0.000 description 1
- 239000000725 suspension Substances 0.000 description 1
- 239000012730 sustained-release form Substances 0.000 description 1
- 235000012222 talc Nutrition 0.000 description 1
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- 125000001984 thiazolidinyl group Chemical group 0.000 description 1
- 238000004809 thin layer chromatography Methods 0.000 description 1
- JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 description 1
- ZIBGPFATKBEMQZ-UHFFFAOYSA-N triethylene glycol Chemical compound OCCOCCOCCO ZIBGPFATKBEMQZ-UHFFFAOYSA-N 0.000 description 1
- PYOKUURKVVELLB-UHFFFAOYSA-N trimethyl orthoformate Chemical group COC(OC)OC PYOKUURKVVELLB-UHFFFAOYSA-N 0.000 description 1
- 230000003424 uricosuric effect Effects 0.000 description 1
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 1
- 229920002554 vinyl polymer Polymers 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D239/00—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings
- C07D239/02—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings
- C07D239/24—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings having three or more double bonds between ring members or between ring members and non-ring members
- C07D239/28—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings having three or more double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, directly attached to ring carbon atoms
- C07D239/46—Two or more oxygen, sulphur or nitrogen atoms
- C07D239/52—Two oxygen atoms
- C07D239/54—Two oxygen atoms as doubly bound oxygen atoms or as unsubstituted hydroxy radicals
- C07D239/545—Two oxygen atoms as doubly bound oxygen atoms or as unsubstituted hydroxy radicals with other hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, directly attached to ring carbon atoms
- C07D239/557—Two oxygen atoms as doubly bound oxygen atoms or as unsubstituted hydroxy radicals with other hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, directly attached to ring carbon atoms with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, directly attached to ring carbon atoms, e.g. orotic acid
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D295/00—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms
- C07D295/04—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms with substituted hydrocarbon radicals attached to ring nitrogen atoms
- C07D295/14—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms with substituted hydrocarbon radicals attached to ring nitrogen atoms substituted by carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals
- C07D295/145—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms with substituted hydrocarbon radicals attached to ring nitrogen atoms substituted by carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals with the ring nitrogen atoms and the carbon atoms with three bonds to hetero atoms attached to the same carbon chain, which is not interrupted by carbocyclic rings
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Thiazole And Isothizaole Compounds (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DK115374A DK115374A (enrdf_load_stackoverflow) | 1974-03-04 | 1974-03-04 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DE2509049A1 true DE2509049A1 (de) | 1975-09-11 |
Family
ID=8101605
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE19752509049 Pending DE2509049A1 (de) | 1974-03-04 | 1975-03-01 | Neue substituierte n-acyl-n''-(3-amino-2-cyano-acryloyl)-formamidrazone, verfahren zu ihrer herstellung und sie enthaltende arzneimittel |
Country Status (4)
| Country | Link |
|---|---|
| BE (1) | BE826258A (enrdf_load_stackoverflow) |
| DE (1) | DE2509049A1 (enrdf_load_stackoverflow) |
| DK (1) | DK115374A (enrdf_load_stackoverflow) |
| FR (1) | FR2262976A1 (enrdf_load_stackoverflow) |
Citations (8)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2608507A (en) | 1949-08-20 | 1952-08-26 | Sharp & Dohme Inc | Dialkyl sulfamyl benzoic acids |
| GB860303A (en) | 1958-06-20 | 1961-02-01 | Ici Ltd | Pharmaceutical compositions comprising ª‡-aryloxy-aliphatic carboxylic acids and/or ª |
| DE1904894U (de) | 1964-03-28 | 1964-11-19 | Karl Dipl Ing Gruendig | Trag- und befestigungsvorrichtung fuer sicherheitsgurte. |
| BE704574A (enrdf_load_stackoverflow) | 1966-10-03 | 1968-04-02 | ||
| BE727754A (enrdf_load_stackoverflow) | 1968-02-02 | 1969-07-31 | ||
| BE739243A (enrdf_load_stackoverflow) | 1968-10-08 | 1970-03-02 | ||
| BE755924A (fr) | 1969-09-12 | 1971-02-15 | Byk Gulden Lomberg Chem Fab | Derives d'acide pyrazole-4-acetique, leur procede de preparation et medicaments en contenant |
| LU66036A1 (enrdf_load_stackoverflow) | 1972-09-08 | 1974-03-14 |
-
1974
- 1974-03-04 DK DK115374A patent/DK115374A/da unknown
-
1975
- 1975-03-01 DE DE19752509049 patent/DE2509049A1/de active Pending
- 1975-03-04 FR FR7506629A patent/FR2262976A1/fr not_active Withdrawn
- 1975-03-04 BE BE153973A patent/BE826258A/xx unknown
Patent Citations (8)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2608507A (en) | 1949-08-20 | 1952-08-26 | Sharp & Dohme Inc | Dialkyl sulfamyl benzoic acids |
| GB860303A (en) | 1958-06-20 | 1961-02-01 | Ici Ltd | Pharmaceutical compositions comprising ª‡-aryloxy-aliphatic carboxylic acids and/or ª |
| DE1904894U (de) | 1964-03-28 | 1964-11-19 | Karl Dipl Ing Gruendig | Trag- und befestigungsvorrichtung fuer sicherheitsgurte. |
| BE704574A (enrdf_load_stackoverflow) | 1966-10-03 | 1968-04-02 | ||
| BE727754A (enrdf_load_stackoverflow) | 1968-02-02 | 1969-07-31 | ||
| BE739243A (enrdf_load_stackoverflow) | 1968-10-08 | 1970-03-02 | ||
| BE755924A (fr) | 1969-09-12 | 1971-02-15 | Byk Gulden Lomberg Chem Fab | Derives d'acide pyrazole-4-acetique, leur procede de preparation et medicaments en contenant |
| LU66036A1 (enrdf_load_stackoverflow) | 1972-09-08 | 1974-03-14 |
Non-Patent Citations (4)
| Title |
|---|
| I.T. Harrison et al., J.Med.Chem. 13 [1970] 203 |
| J.W. Scheeren und W. Stevens, Rec. 85 [1966] 793 |
| L.O. Ross et al. in J.Org.Chem. 25 [1960], 1950 - 1953 |
| S. Ratner, H.T. Clarke, J.Am.Chem.Soc. 59, [1937] 200 |
Also Published As
| Publication number | Publication date |
|---|---|
| DK115374A (enrdf_load_stackoverflow) | 1975-11-03 |
| FR2262976A1 (en) | 1975-10-03 |
| BE826258A (fr) | 1975-09-04 |
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